Transition Metal-Free Cross-Dehydrogenative Coupling Reaction of Coumarins with Acetonitrile or Acetone.

J Org Chem

Department of Chemistry , Nanchang University, No. 999, Xuefu Road , Nanchang 330031 , P. R. China.

Published: November 2018

A transition metal-free cross-dehydrogenative coupling of coumarins with acetonitrile or acetone has been established. A series of coumarins were subjected to reaction with acetonitrile or acetone in the presence of tert-butyl benzoperoxoate and potassium fluoride for direct synthesis of 3-cyanomethyl (or acetomethyl) coumarins. The method exhibits good functional group tolerance, and desired products were obtained in moderate to good yields. Meanwhile, a radical pathway was proposed to describe the cross-dehydrogenative coupling of coumarins with acetonitrile.

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http://dx.doi.org/10.1021/acs.joc.8b01508DOI Listing

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